| 1 | Tue 12 Sep 2023 | 41-1 v Hungerford TownHungerford Town 1-1 Dorchester Town | Southern League - Premier South |
| 2 | Sat 23 Sep 2023 | 223-1 v Didcot TownDorchester Town 3-1 Didcot Town | Southern League - Premier South |
| 3 | Tue 26 Sep 2023 | 220-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 4 | Sat 7 Oct 2023 | 22 1-3 v Merthyr TownMerthyr Town 3-1 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 5 | Wed 11 Oct 2023 | 222-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 6 | Tue 24 Oct 2023 | 221-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 7 | Sat 28 Oct 2023 | 22 1-1 v Hayes & Yeading UnitedDorchester Town 1-1 Hayes & Yeading United | Southern League - Premier South |
| 8 | Sat 25 Nov 2023 | 222-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 9 | Sat 9 Dec 2023 | 222-1 v Swindon SupermarineSwindon Supermarine 1-2 Dorchester Town | Southern League - Premier South |
| 10 | Sat 16 Dec 2023 | 221-2 v Walton & HershamDorchester Town 1-2 Walton & Hersham | Southern League - Premier South |
| 11 | Sat 23 Dec 2023 | 60-2 v Chesham UnitedChesham United 2-0 Dorchester Town | Southern League - Premier South |
| 12 | Tue 26 Dec 2023 | 221-2 v Poole TownDorchester Town 1-2 Poole Town | Southern League - Premier South |
| 13 | Sat 6 Jan 2024 | 202-4 v Hungerford TownDorchester Town 2-4 Hungerford Town | Southern League - Premier South |
| 14 | Sat 13 Jan 2024 | 202-0 v Harrow BoroughHarrow Borough 0-2 Dorchester Town | Southern League - Premier South |
| 15 | Sat 20 Jan 2024 | 203-2 v Merthyr TownDorchester Town 3-2 Merthyr Town | Southern League - Premier South |
| 16 | Sat 27 Jan 2024 | 200-0 v Plymouth ParkwayDorchester Town 0-0 Plymouth Parkway | Southern League - Premier South |
| 17 | Sat 3 Feb 2024 | 201-0 v Didcot TownDidcot Town 0-1 Dorchester Town | Southern League - Premier South |
| 18 | Tue 6 Feb 2024 | 20 1-1 v Hanwell TownHanwell Town 1-1 Dorchester Town | Southern League - Premier South |
| 19 | Sat 10 Feb 2024 | 200-3 v Gosport BoroughDorchester Town 0-3 Gosport Borough | Southern League - Premier South |
| 20 | Sat 17 Feb 2024 | 203-1 v Bracknell TownBracknell Town 1-3 Dorchester Town | Southern League - Premier South |
| 21 | Sat 24 Feb 2024 | 202-2 v HendonDorchester Town 2-2 Hendon | Southern League - Premier South |
| 22 | Wed 28 Feb 2024 | 204-4 v AFC TottonAFC Totton 4-4 Dorchester Town | Southern League - Premier South |
| 23 | Sat 9 Mar 2024 | 202-1 v Beaconsfield TownDorchester Town 2-1 Beaconsfield Town | Southern League - Premier South |
| 24 | Sat 16 Mar 2024 | 204-3 v Beaconsfield TownBeaconsfield Town 3-4 Dorchester Town | Southern League - Premier South |
| 25 | Sat 23 Mar 2024 | 201-0 v SalisburyDorchester Town 1-0 Salisbury | Southern League - Premier South |
| 26 | Sat 30 Mar 2024 | 20 1-1 v Winchester CityWinchester City 1-1 Dorchester Town | Southern League - Premier South |
| 27 | Mon 1 Apr 2024 | 202-1 v Tiverton TownDorchester Town 2-1 Tiverton Town | Southern League - Premier South |
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